scholarly journals Studies on the Reactions of Heterocyclic Compounds. VIII. 1, 3-Dipolar Cycloaddition Reaction of Isoquinolinium Cyano (methoxycarbonyl)-methylide with Dimethyl Acetylenedicarboxylate : Structure and Reaction of the Adduct

1972 ◽  
Vol 20 (8) ◽  
pp. 1809-1814 ◽  
Author(s):  
TERUO KUTSUMA ◽  
KAZUO FUJIYAMA ◽  
YOSHIRO KOBAYASHI
Keyword(s):  
Heterocyclic Compounds ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Dimethyl Acetylenedicarboxylate

1,3-Dipolar Cycloaddition Reaction of Dimethyl Acetylenedicarboxylate with Hydrazones

Heterocycles ◽  
1974 ◽  
Vol 2 (2) ◽  
pp. 280 ◽  
Author(s):  
Haruo Ogura ◽  
Hiroshi Takahashi ◽  
Kazuo Kubo ◽  
Kozo Ogawa ◽  
Hitomi Sakai
Keyword(s):  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Dimethyl Acetylenedicarboxylate

scholarly journals Huisgen [3 + 2] Dipolar Cycloadditions of Phthalazinium Ylides to Activated Symmetric and Non-Symmetric Alkynes

Molecules ◽  
2020 ◽  
Vol 25 (19) ◽  
pp. 4416
Author(s):  
Vasilichia Antoci ◽  
Costel Moldoveanu ◽  
Ramona Danac ◽  
Violeta Mangalagiu ◽  
Gheorghita Zbancioc
Keyword(s):  
Reaction Time ◽  
Comparative Study ◽  
Cycloaddition Reaction ◽  
Environmentally Friendly ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Dimethyl Acetylenedicarboxylate ◽  
Thermal Heating ◽  
Dipolar Cycloadditions ◽  
Methyl Propiolate

We present herein a straightforward and efficient pathway for the synthesis of pyrrolophthalazine cycloadducts via Huisgen [3 + 2] dipolar cycloaddition reactions of phthalazinium ylides to methyl propiolate or dimethyl acetylenedicarboxylate (DMAD). A thoroughly comparative study concerning the efficiency of synthesis, conventional thermal heating (TH) versus microwave (MW) and ultrasound (US) irradiation, has been performed. The cycloaddition reactions of phthalazinium ylides to methyl propiolate occur regiospecific, with a single regioisomer being obtained. Under conventional TH, the cycloaddition reaction of phthalazinium ylides with DMAD occurs to a mixture of inseparable partial and fully aromatized pyrrolophthalazine cycloadducts, while MW or US irradiation are leading only to fully aromatized compounds, with the reactions becoming selective. A feasible mechanism for formation of fully aromatized compounds is presented. Besides selectivity, it has to be noticed that the reaction setup under MW or US irradiation offer a number of other certain advantages: higher yields, decreasing of the amount of used solvent comparative with TH, decreasing of the reaction time from hours to minutes and decreasing of the consumed energy; consequently, these reactions could be considered environmentally friendly.

Synthesis of New Hexakis-Heterocyclic Compounds and their Use in the Formation and Stabilization of Au and Ag Nanoparticles

2014 ◽  
Vol 976 ◽  
pp. 3-7
Author(s):  
María Isabel Montalvo-Sierra ◽  
Miriam A. Martins Alho ◽  
Ana María Herrera-Gonzalez ◽  
Jesús García-Serrano ◽  
Paola Belem Bocardo-Tovar
Keyword(s):  
Ir Spectroscopy ◽  
Ag Nanoparticles ◽  
Heterocyclic Compounds ◽  
Cyano Group ◽  
Cycloaddition Reaction ◽  
Aldehyde Group ◽  
Dipolar Cycloaddition ◽  
Vis Spectroscopy ◽  
Aldehyde Derivative

The stabilization of nanoparticles in solution is a challenge of major proportions, and avoiding the formation of aggregates and eventual coalescence of particles is directly linked to the conservation of its unique properties. In this work, we reported the synthesis of two hexakis-heterocyclic compounds, containing the tetrazole or 2-amino-1,3,4-thiadiazole group, respectively. The hexa-heterocyclic compounds were used in the synthesis and stabilization of Au and Ag nanoparticles. To obtain these molecules was used phosphonitrilic chloride trimer compound as core, which reacted with phenols properly substituted in theparaposition with either cyano or aldehyde group. The cyano group was successfully converted to the corresponding tetrazole using a 1,3-dipolar cycloaddition reaction with ammonium azide generatedin situ. In the case of aldehyde derivative, it was converted to the corresponding thiosemicarbazone, which was further cyclized using FeCl3. Compounds were characterized by RMN and IR spectroscopy. The UV-Vis spectroscopy was used for nanoparticles analysis.

1,3-Dipolar cycloadditions of ylide of 5-nitro-2-furfurylpyridinium bromide in indolizine synthesis

1982 ◽  
Vol 47 (6) ◽  
pp. 1738-1745 ◽  
Author(s):  
Jarmila Štetinová ◽  
Miloslava Dandárová ◽  
Jaroslav Kováč ◽  
Darina Mesárošová ◽  
Ján Leško
Keyword(s):  
Mass Spectra ◽  
Cycloaddition Reaction ◽  
Ethyl Acrylate ◽  
Dipolar Cycloaddition ◽  
Dimethyl Acetylenedicarboxylate ◽  
Diethyl Maleate ◽  
Dipolar Cycloadditions ◽  
H Nmr

Substituted 3-(5-nitro-2-furyl)indolizines III-X were synthesized by 1,3-dipolar cycloaddition reaction of the ylide II, generated from 5-nitro-2-furfurylpyridinium bromide (I), with acrylonitrile, ethyl acrylate, diethyl maleate, benzalacetophenone, ethyl 3-(5-nitro-2-furyl)acrylate, (5-nitro-2-furfurylidene)acetophenone, β-nitrostyrene and dimethyl acetylenedicarboxylate. The structure of these products is discussed on the basis of their 1H NMR and mass spectra.

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